I work for a major healthcare provider and we hired folks with not-so-clean backgrounds as long as they're disclosed. If you do not disclose any issue and it comes out that you did find something, you can either 1) appeal the decision by reviewing the background check with our provider or 2) wait a full year before reapplying again.

Background checks are not perfect, we know. That's why when you apply, you have the right to get a full report for free. I always recommend checking that box to get it when applying. That way, if something comes up, you can dispute it with the background check agency, and it's very easy.

What would you advise for smaller companies that don't background check? Or if I don't fill out an application and get an interview? Do I still bring it up and if so, when is it appropriate?

If you know for sure that they don't do background checks, then don't include any information that may hurt your chances. After all, you are a human resource, not a friend of a company.

Really depends on where you work. In SF, it's pretty amenable to that. A smart friendly co-worker had gotten locked up for drugs a few years before he started, even warning the HR department that his background check wouldn't come up clean, and that'd been no problem at all, and he's since moved gigs. (If you'd like an intro just hit me up :-) and I'll see what I can do)

Cali is too far for me, thanks for the offer though :) Hope to find people like you in the south east!

Does expungement not apply to your case? I know some teenage criminals get their records cleared.

No, I have federal drug charges, and I embellished a little on "teenager". I was 18-19 which technically is an adult. I have this background forever.